Phenyl beta-nitrostyryl sulfides



United States Patent Office 3,394,191 Patented July 23, 1968 3,394,191 PHENYL fl-NITROSTYRYL SULFIDES Marvin L. ()ftedahl, Crestwood, Mo., assignor to Monsanto Company, St. Louis, Mo., a corporation of Delaware No Drawing. Filed Feb. 9, 1966, Ser. No. 526,078 8 Claims. (Cl. 260609) eral formula where X is selected from a group consisting of chlorine, bromine, CF and N and n is an integer from 0 to 3; Y is selected from a group consisting of chlorine, bromine, N0 and m is an integer from 0 to 3; and the sum of m-i-n is at least one.

This class of compounds can be prepared by reacting a suitable benzenesulfenyl halide with a suitable fi-nitrostyrene in a solvent such as acetic acid. The reactants are usually heated to the reflux temperature of the solvent, although the reaction may be carried out at room temperature. After the reaction is complete, the mixture is poured into ice water and the precipitate recovered.

A typical illustrative reaction for preparing a compound of this invention is shown in the following equation:

01 CH=CHNO2 The invention will be more fully understood by reference to the following examples which are set forth herein solely for the purpose of illustration, and which are not to be construed as limiting the scope of the present in vention.

Example 1 Example 2 Following the detailed procedure set forth in Example 1, the reactants employed are 4.47 grams (0.02 mol) of p-bromobenzenesulfenyl chloride and 4.56 grams (0.02 mol) of m-bromo-flmitrostyrene. The product obtained is fi-(p-bromophenylthio)-fi-nitro-m-bromostyrene.

Example 3 Following the detailed procedure set forth in Example 1, the reactants employed are 4.69 grams (0.02 mol) of 2,4-dinitrobenzenesulfenyl chloride and 6.14 grams (0.02 mol) of 3,4-dibromo-;3-nitrostyrene. The product obtained is ,8 (2,4 dinitrophenylthio)-;3-nitro-3,4-dibromo styrene.

Example 4 Following the detailed procedure set forth in Example 1, the reactants employed are 4.97 grams (0.02 mol) of 3,4,5-trichlorobenzenesulfenyl chloride and 4.34 grams (0.02 mol) of m-trifluoromethyl-B-nitrostyrene. The product obtained is fi-(3,4,5-trichlorophenylthio)-;8-nitro-mtrifluoromethylstyrene.

Example 5 Following the detailed procedure set forth in Example 1, the reactants employed are 2.89 grams (0.02 mol) of benzenesulphenyl chloride and 4.34 grams (0.02 mol) of m-trifluoromethyl fl-nitrostyrene. The product obtained is ,6- phenylthio -,8-nitro-m-trifluoromethylstyrene.

Example 6 Following the detailed procedure set forth in Example 1, the reactants employed are 4.97 grams (0.02 mol) of 3,4,5-trichlorobenzenesulphenyl chloride and 6.14 grams (0.02 mol) of 3,4-dibromo-B-nitrostyrene. The product obtained is B (3,4,5 trichlorophenylthio)-/8-nitro-3,4-dibromostyrene.

The products of the present invention are useful microbiocides adapted for use in the control of bacterial and fungal organisms. In a representative test, ,B-(p-chlorophenylthio)- 3-nitro-3,4-dichlorostyrene is found to be active against Staphylococcus aureus, Salmonella typhosa and Aspergillus niger at a dilution of one part per one hundred-thousand respectively. Similar activity is displayed by other and different phenyl ,B-nitrostyryl sulfides of this invention.

While the invention has been described herein by means of several specific examples, it is not so limited. It is to be understood that modifications and variations of the invention, obvious to those skilled in the art, may be made without departing from the spirit and scope of said invention.

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:

1. A compound of the formula where X is selected from a group consisting of chlorine, bromine, CF and N0 and n is an integer from 0 to 3; Y is selected from a group consisting of chlorine, bromine and N0 and m is an integer from 0 to 3; and the sum of m+n is at least one.

2. An invention as defined in claim 1 wherein X and Y are each chlorine.

3. An invention as defined in claim 1 wherein X and Y are each bromine.

4. An invention as defined in claim 1 wherein X and Y are each N0 5. An invention as defined in claim 1 wherein X and Y are each CF 3 4 6. An invention as defined in claim 1 wherein the References Cited compound is fi(p'chlorophenylthio)'fi'nitro'34dich1mo' Brookes et 211.: Chemical Abstracts, vol. 52, p. 4543 styrene. I (1952) An Invention as defined damn I Wherem the Kharasch et 2.1.: Chemical Abstracts vol. 60 p. 15 700 pound is ,8-(p-trifluoromethylphenylthio)-B-nitro-3,4-di- 5 (1964) chlorostyrene.

8. An invention as defined in claim 1 vherem the corn- CHARLES R PARKER Primary Examiner pound is [3 (p bromophenylthio)-/3-n1tro-3,4-dibromostyrene. D. R. PHILLIPS, Assistant Examiner. 

1. A COMPOUND OF THE FORMULA 